54 Best Sights in The Loop, including the West Loop and South Loop, Chicago

Built in 1888 as the home of the Franklin Company, one of the largest printers at the time, this building has intricate decoration. The tile work on the facade leads up to The First Impression—a medieval scene illustrating the first application of the printer's craft. Above the entryway is a motto: "The excellence of every art must consist in the complete accomplishment of its purpose." The building was turned into condos in 1989.

A bustling center for food processing and distribution as recently as the 2000s, this former industrial district transformed into an upscale stretch of gleaming corporate offices, luxury condos, and Michelin-star restaurants with remarkable speed. The last of the seafood, produce, and meatpacking plants were gone by the end of the 2010s; Fulton Market is now a full-on dining and nightlife destination.

Bordered by Lake Michigan to the east, a spectacular skyline to the west, and the Museum Campus to the south, Grant Park serves as the city's front yard and unofficial gathering place. This pristine open space has walking paths, a stand of stately elm trees, and formal rose gardens, where Loop dwellers and 9-to-5-ers take refuge from the concrete and steel. It also hosts many of the city's largest outdoor events, including the annual Taste of Chicago, a vast picnic featuring foods from more than 70 restaurants.

The park's centerpiece is the gorgeous, tiered Buckingham Fountain (between Columbus and Lake Shore Drives, east of Congress Plaza), which has intricate pink-marble seashell designs, water-spouting fish, and bronze sculptures of sea horses. Built in 1927, it was patterned after one at Versailles but is about twice the size. See the fountain in all its glory between early May and mid-October, when it's elaborately illuminated at night and sprays colorfully lighted waters. Linger long enough to experience the spectacular display that takes place every hour on the hour, and you'll witness the center jet of water shoot 150 feet into the air.

This small strip may as well be half a world away from the rest of the West Loop. Greek restaurants are the main draw here. Continue west on Madison, past the slew of new condo developments and vintage conversions in progress, and you'll come to one of Chicago's popular dining and nightlife destinations. On a stretch of Madison roughly between Sangamon and Elizabeth streets, you'll find boutiques, trendy bars and lounges, and popular restaurants. The National Hellenic Museum, at 333 South Halsted, explores the Greek immigrant experience and the influence of Greek culture.

Opened in 1991 and named for Chicago's first African American mayor, this library was primarily designed by architect Thomas Beeby, of Hammond, Beeby & Babka. Gargantuan and almost goofy, the granite-and-brick edifice is a uniquely postmodern homage to Chicago's great architectural past. The heavy, rusticated ground level recalls The Rookery; the stepped-back, arched windows are a reference to the great arches in the Auditorium Theatre; the swirling terra-cotta design is pinched from the Marquette Building; and the glass curtain wall on the west side is a nod to 1950s modernism. The huge, gargoyle-like sculptures atop the building include owls, a symbol of wisdom. The excellent Children's Library, an 18,000-square-foot haven on the second floor, has vibrant wall-mounted figures by Chicago imagist Karl Wirsum. Works by noted Chicago artists are displayed along a second-floor walkway above the main lobby. There's also an impressive Winter Garden with skylights on the ninth floor. Free programs and performances are offered regularly.

A runt compared to today's tall buildings, this sparkling 19-story high-rise from Skidmore, Owings & Merrill was a trailblazer when it was built in the late 1950s. It was the first skyscraper erected with external supports (allowing for wide-open, unobstructed floors within), the first to employ steel pilings (driven 85 feet down to bedrock), the first in the Loop to be fully air-conditioned, and the first to feature underground parking.

An opulent "hasheesh-dream decor" of Buddhas and elephant-type chairs made the erstwhile Oriental Theatre a popular spot for viewing first-run movies starting in 1926. Though listed on the National Register of Historic Places in 1978, the building continued to crumble for some time after. In 1998 it was restored to its past splendor and since then has had a second life as a home to Broadway shows; it was rechristened for the late patriarch of the Nederlander family of theater producers in 2019.

This neoclassical building, designed by Daniel Burnham, opened in 1907 as one of the world's earliest department stores, Marshall Field's. Macy's acquired the chain in 2005 and changed the store's name. An uproar ensued, and many Chicagoans still refer to the flagship as Marshall Field's. A visit is as much an architectural experience as a retail one. The building has distinct courtyards (one resembling an Italian palazzo), a striking Tiffany dome of mosaic glass, a calming fountain, and gilded pillars. Its green clock at the State and Randolph entrance is a Chicago landmark. For lunch, try the Walnut Room, and make sure to sample Frango mints—the store's specialty, they were once made on the 13th floor.

Named after former Mayor Richard M. Daley's late wife, this park offers a place to play between Lake Michigan and the city's skyline. Opened in late 2014, it includes 40-foot-high rock-climbing sculptures, an Enchanted Forest with a kaleidoscope and mirrored maze, a Slide Crater, a Wave Lawn, and an area strictly for toddlers. A skating ribbon winds around the park, with ice skates available to rent in the winter months, and rollerblades and scooters in the summer.

Like a slipcover over a sofa, the clean, geometric facade of this 1895 building expresses what lies beneath: in this case, a structural steel frame. Sure, the base is marked with roughly cut stone and a fancy cornice crowns the top, but the bulk of the Marquette Building mirrors the cage around which it is built. Inside is another story. The intimate lobby is a jewel box of a space, where a single Doric column stands surrounded by a Tiffany glass mosaic depicting the exploits of French Jesuit missionary Jacques Marquette, an early explorer of Illinois and the Upper Midwest. From its steel skeleton to the terra-cotta ornamentation, this Holabird & Roche structure is a clear example of the Chicago style.

Built in two segments a few years apart, the Monadnock captures the turning point in high-rise construction. Its northern half, designed in 1891 by Burnham & Root, was erected with traditional load-bearing masonry walls (6 feet deep at the base). In 1893 Holabird & Roche designed its southern half, which rose around the soon-to-be-common steel skeleton. The building's stone-and-brick exterior, shockingly unornamented for its time, led one critic to liken it to a chimney. The lobby is equally spartan; lined on either side with windowed shops, it's essentially a corridor, but one well worth traveling. Walk it from end to end and you'll feel as if you're stepping back in time.

"Contemporary" is generally defined here as work made in the past two or three decades. Curators constantly seek out new talent and underappreciated established photographers, which means that there are artists here you probably won't see elsewhere. Rotating exhibits have included explorations of infrastructure, crime, and American identity.

Part of the Museum Campus, Northerly Island is a man-made peninsula in Lake Michigan. It's home to the Adler Planetarium as well as a 40-acre park, with walking and biking trails and the 12th Street Beach.

Built in 1891, the simple, redbrick Pontiac is an early Chicago School skyscraper—note the classic rectangular shape and flat roof. It is the city’s oldest existing Holabird & Roche building.

Bounded by Ida B. Wells Drive on the north, Polk Street on the south, Plymouth Court to the east, and the Chicago River to the west, this district fell into disrepair in the 1960s, but a neighborhood resurgence began in the late 1970s. Bibliophiles flock in for the Printers Row Lit Fest, a weekend-long literary celebration held each September. But, at any time of year, you can admire examples of buildings by the group that represented the First Chicago School of Architecture (including Louis Sullivan).

There are two architecturally notable buildings at the plaza. Directly west of the Aon Center and across from Millennium Park is One Prudential Plaza. Designed by Alfonso Iannelli and completed in 1955, this limestone-and-ridged-aluminum structure was once the city's tallest building (barring the statue of Ceres atop the Board of Trade). At the time, it had the world's fastest elevators and an observation deck that became passé once some of the city's other behemoths were completed. Attached to One Prudential is its sibling Two Prudential Plaza, nicknamed "Two Pru," a towering glass-and-granite giant with an address of 180 North Stetson Avenue. Along with their neighbors they form a block-long business-oriented minicity. Two Prudential is the tallest reinforced concrete building in the city, and its blue detailing and beveled roof are instantly recognizable from afar.

This famed indoor-outdoor flea market, held on the last Saturday and Sunday of the month from late March through mid-December, is Chicago's answer to London's Portobello Road Market. Centered on Randolph Street and Ogden Avenue at Plumber's Hall, it offers midcentury furniture, vintage handbags, ephemera, and much more. May through September, free shuttles head back and forth between the Hall and Water Tower Place on the hour, from 10 to 3.

The clearly expressed, gleaming verticality that characterizes the modern skyscraper was first and most eloquently articulated in this trailblazing steel-frame tower, built by Burnham, Root, and Charles Atwood. Completed in 1895 and now home to the stylish Staypineapple Hotel, the building was a crumbling eyesore until the late 1990s, when the city initiated a major restoration. In the early and mid-1900s, it was a mixed-use office building. Al Capone's dentist reportedly worked out of what's now Room 809. Don't be misled when you go looking for this masterpiece—a block away, at State and Randolph streets, a dormitory for the School of the Art Institute of Chicago shamelessly mimics it. Once you've found the real thing, admire the mosaic floor and ironwork in the reconstructed elevator lobby. The building boasts early examples of the Chicago Window, which define the entire facade by adding a shimmer and glimmer to the surrounding white terra-cotta.

Named for late mayor Richard J. Daley, this boldly plain high-rise is the headquarters of the Cook County court system, but it's best known as the site of a sculpture by Picasso. Simply dubbed the Picasso, this monumental piece provoked an outcry when it was installed in 1967; baffled Chicagoans tried to determine whether it represented a woman or an Afghan hound. In the end, they gave up guessing and simply embraced it as a unique symbol of the city. The building itself was constructed in 1965 of Cor-Ten steel, which weathers naturally to an attractive bronze. In summer, its plaza is the site of concerts, political rallies, and a Thursday farmers' market. In December, Christkindlmarket (a traditional German market selling food and gifts) takes over the area.

Opened in 1924 as the Municipal Grant Park Stadium, the facility was renamed in 1925 to commemorate American soldiers who died during World War I. Just south of the Museum Campus, the building and its massive columns are reminiscent of ancient Greece. It's the home field for the NFL's Chicago Bears and Major League Soccer's Chicago Fire FC, as well as a venue for college games and concerts. A controversial modern glass expansion, which looks like a spaceship that landed on the arena, was completed in 2003. Behind-the-scenes tours feature the Doughboy statue, Colonnades, the field, South Courtyard, visitors' locker room, the suites, and the United Club.

From 1899 to 2007 this was the flagship location for the department store Carson, Pirie, Scott & Co. The work of one of Chicago's most renowned architects, it combines Louis H. Sullivan's visionary expression of modern design with intricate cast-iron ornamentation. The eye-catching rotunda and the 11 stories above it are actually an addition Sullivan made to his original building. In later years D.H. Burnham & Co. and Holabird & Root extended Sullivan's smooth, horizontal scheme farther down State Street. The ground floor now houses a Target, with office tenants occupying the floors above.

Now home to the acclaimed Chicago Symphony Orchestra (CSO), this complex includes Orchestra Hall, built in 1904 under the supervision of Daniel Burnham. The Georgian building has a symmetrical facade of pink brick with limestone quoins, lintels, and other decorative elements. An interior renovation, completed in 1997, added a seating area that is behind and above the stage, allowing patrons a unique vantage point.

This 50,000-square-foot food hall sports a rotating roster of counter-service stalls, representing 18 hand-picked Chicago eateries. Collected under one roof along with three bars, an outdoor terrace, and a working demo kitchen for chef-driven classes, it's a sort of EPCOT Center of Chicago food for those who don't have time to visit many different neighborhoods.

Running along both sides of Wabash Avenue from Ida B. Wells Drive south to 16th Street, this mile-long stretch is an outdoor gallery of murals and street art. There are nearly 40 permanent installations and an evolving set of temporary exhibitions. Chicago artists including Shepard Fairey, Hebru Brantley, and Sam Kirk have had work shown here.